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Details

Stereochemistry ABSOLUTE
Molecular Formula C33H35FO8
Molecular Weight 578.6246
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIAMCINOLONE FURETONIDE

SMILES

[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)COC(=O)C6=CC7=C(O6)C=CC=C7

InChI

InChIKey=OSWKQSQWSQSPQH-GNFRAIDCSA-N
InChI=1S/C33H35FO8/c1-29(2)41-27-15-22-21-10-9-19-14-20(35)11-12-30(19,3)32(21,34)25(36)16-31(22,4)33(27,42-29)26(37)17-39-28(38)24-13-18-7-5-6-8-23(18)40-24/h5-8,11-14,21-22,25,27,36H,9-10,15-17H2,1-4H3/t21-,22-,25-,27+,30-,31-,32-,33+/m0/s1

HIDE SMILES / InChI

Description

Triamcinolone acetonide is a synthetic corticosteroid used to treat various skin conditions, and to relieve the discomfort of mouth sores. In nasal spray form, it is used to treat allergic rhinitis. It is a more potent derivative of triamcinolone, and is about eight times as potent as prednisone. TRIESENCE™ is a synthetic corticosteroid indicated for: sympathetic ophthalmia, temporal arteritis, uveitis, and ocular inflammatory conditions unresponsive to topical corticosteroids. Triamcinolone acetonide is a synthetic fluorinated corticosteroid with approximately 8 times the potency of prednisone in animal models of inflammation. Although the precise mechanism of corticosteroid antiallergic action is unknown, corticosteroids have been shown to have a wide range of actions on multiple cell types (e.g., mast cells, eosinophils, neutrophils, macrophages, lymphocytes) and mediators (e.g., histamine, eicosanoids, leukotrienes, cytokines) involved in inflammation.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRIESENCE
Primary
TRIESENCE
Primary
TRIESENCE
Primary
Nasacort
Primary
Nasacort

Cmax

ValueDoseCo-administeredAnalytePopulation
10.5 ng/mL
5 mg single, oral
TRIAMCINOLONE ACETONIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
30.4 ng × h/mL
5 mg single, oral
TRIAMCINOLONE ACETONIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
, respiratory
TRIAMCINOLONE ACETONIDE plasma
Homo sapiens
2.6 h
5 mg single, oral
TRIAMCINOLONE ACETONIDE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
29%
, respiratory
TRIAMCINOLONE ACETONIDE plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
40 mg/mL
Route of Administration: Other
In Vitro Use Guide
In chondrocyte cultures, triamcinolone acetonide (TA) reduced chondrocyte viability in a concentration-dependent manner. Low-molecular-weight hyaluronan (LMWHA) 2.5 mg/ml combined with TA at IC20 (0.09 mg/ml) could increase the viability of normal chondrocytes when compared with TA-treated alone. TA at IC20 induced down-regulation of ACAN and induced up-regulation of ADAMTS5 in canine normal chondrocytes. TA at IC20 (0.11 mg/ml) up-regulated ADAMTS5, MMP2, MMP3, MMP13, and ACAN expression in canine OA chondrocytes. In explant culture, TA at 1.25, 2.5, and 5 mg/ml increased the severity of structural damage, chondrocyte loss and cluster formation, and proteoglycan loss in OA cartilage.